CN105007985A - Compositions and methods for treating damaged hair - Google Patents

Abstract

Compositions and methods are disclosed for repairing damaged keratin fibers or otherwise strengthening keratin fibers, including hair of the human scalp, and particularly hair that has been damaged chemically, physically, thermally or by other means. The compositions comprise 3,3'-thiodipropionic acid (TDPA) or a derivative thereof in a cosmetically acceptable vehicle.

Description

Compositions and methods for treating damaged hair

Cross References to Related Applications

This patent application claims priority to US Patent Application Serial No. 61/774,132, filed March 7, 2013. The entire contents of the aforementioned applications are incorporated herein by reference.

technical field

The present invention relates to methods and compositions for strengthening keratin fibers and for repairing damaged keratin fibers. In particular, the present invention relates to hair care compositions, such as shampoos and conditioners, comprising an effective amount of 3,3'-thiodipropionic acid (TDPA) or derivatives thereof for strengthening and repairing damaged scalp hair.

Background technique

A wide variety of products and treatments are available to the consumer to improve the appearance of human hair, including hair dyes, lighteners or bleaches, permanent treatments, and the like. Some treatments employ harmful chemicals or heat, which can damage and weaken human hair. Even less harmful treatments including blow drying or even brushing or combing or hair can cause damage over time. Exposure to excess UV radiation from the sun and environmental damage, including chemicals in swimming pools, can also damage hair. The cumulative result of these factors is often dry, brittle hair that is prone to breakage or split ends.

There is a need for compositions that enhance hair to prevent or remediate chemical, mechanical and environmental damage. It is therefore an object of the present invention to provide compositions, including shampoos and conditioners, which strengthen and repair damaged scalp hair. A further object of the present invention is to provide a treatment regimen for preventing or correcting damage to hair, especially hair that has been artificially colored or lightened.

Contents of the invention

In accordance with the foregoing and other objects, the present invention provides methods and compositions for preventing, reversing, correcting and/or arresting damage to human scalp hair, especially hair that has previously been artificially colored or lightened. In one aspect of the present invention, there is provided a composition comprising an effective amount of a compound having the structure represented by formula (I) in a topically acceptable carrier.

Wherein X is selected from -O-, -S-, -CH ₂ -, -NH- or -NR ^N - (where R ^N is methyl or ethyl), but usually should be -S-, and R ₁ and R ₂ are independently selected from hydrogen, C _1-22 hydrocarbyl groups, and cations (eg, ammonium, quaternary ammonium, alkali or alkaline earth metals, etc.). In certain embodiments, X is -S-, R ₁ and R ₂ are hydrogen, and the compound of formula (I) is 3,3'-thiodipropionic acid (TDPA). In certain embodiments, R ₁ and/or R ₂ are independently selected from C _1-20 hydrocarbyl. In certain embodiments, R ₁ and/or R ₂ are independently selected from C _1-15 hydrocarbyl. In certain embodiments, R ₁ and/or R ₂ are independently selected from C _1-10 hydrocarbyl groups. In certain embodiments, R ₁ and/or R ₂ are independently selected from C _1-5 hydrocarbyl.

In one aspect of the invention there is provided a hair care product comprising an effective amount of a compound of formula (I) (eg TDPA) in a topically acceptable carrier such as an aqueous solution or emulsion. In certain embodiments, the hair care product is a conditioner, either of the rinse-off or leave-in variety.

In other aspects, there is provided a method of treating hair comprising applying to said hair at least once a week, more usually at least once a day, a composition comprising an effective amount of a compound of formula (I), such as TDPA, sufficient to reveal the hair's Time to improvement in strength (eg, tensile strength, resistance to breakage and/or minor split-ends, etc.) or overall aesthetic appearance of the hair. The duration of treatment should generally be at least five days, more usually at least one or two weeks, or longer.

These and other aspects will become apparent to those skilled in the art from a reading of the following detailed description of the invention, including the appended claims.

Description of drawings

Figure 1 illustrates the tensile (tensile) load required to break untreated, vehicle-treated or vehicle+TDPA-treated hair fibers.

A detailed description

All amounts provided in weight percent are relative to the overall composition unless otherwise indicated. Unless otherwise specified, the term "alkyl" is meant to encompass straight chain, branched chain, or cyclic hydrocarbon groups, especially those having 1 to 20 carbon atoms, more particularly C _1-12 hydrocarbon groups.

The term "keratin fibers" as used herein includes hair of the scalp, eyelashes, eyebrows, facial hair and body hair (such as hair on arms, legs, etc.). Keratin fibers are not limited to humans, but include any keratin fibers from mammals, such as pet hair and mammalian fur.

Compounds of the present invention generally have a structure shown in formula (I):

In the compound of formula (I), X is selected from -O-, -S-, -CH ₂ -, -NH- or -NR ^N - (where R ^N is methyl or ethyl), but usually should be - S–.

Typically, R and R are independently selected from _hydrogen , C _{1-22 hydrocarbyl} groups, and cations (eg, ammonium, quaternary ammonium, alkali or alkaline earth metals, etc.). _In certain embodiments, R and/or R are _hydrogen . _In the case where R1 and R2 are _hydrogen , the compound of formula (I) is 3,3'-thiodipropionic acid (TDPA). Salts of TDPA are also contemplated, including those in which one or both of the carboxylic acids are ionized. Cosmetically acceptable counterions (ie, cations) are usually, but not necessarily, formed by acid addition reactions with pH adjusting agents such as sodium hydroxide, triethanolamine, and the like.

_In certain embodiments, R and/or R are C _1-22 hydrocarbyl groups, including _but not limited to, alkyl, alkenyl (e.g., vinyl, allyl, etc.), alkynyl, aryl (e.g., phenyl), alkyl-aryl (such as benzyl), aryl-alkyl (such as methylphenyl), heteroaryl, and combinations thereof. The C _1-22 hydrocarbyl group may be substituted with 1-10 heteroatoms such as halogen, oxygen, nitrogen and sulfur. Thus, R and R may comprise halo ₍ perfluoro, etc. ₎ , hydroxyl, alkoxy, epoxy, carboxy, oxa, oxo, ether, ester, amino or amido, Examples include, but are not limited to, groups of the form -(RO) _n- , where R is ethyl or propyl, and n is an integer from 1 to 10. In _one embodiment, R and/or R are alkyl or alkenyl (linear chained, branched or straight chained) having 1-22 carbon atoms or _2-18 carbon atoms ), including, but not limited to, C ₈ (e.g., octanoyl), C ₁₀ (e.g., decanoyl), C ₁₂ (e.g., lauryl), C ₁₄ (e.g., myristyl), C ₁₆ (e.g., cetyl Waxyl), C ₁₈ (eg, stearyl), C ₂₀ (eg, eicosyl) and C ₂₂ (eg, behenyl) alkyl or alkenyl. _{In one} embodiment, R and/or R are lauryl. The compound may be a monoester or a diester of TDPA (or salt) or TDPA.

3,3'-thiodipropionic acid (TDPA) is a compound of formula (I) wherein X is -S- and R ₁ and R ₂ are each hydrogen. Other compounds of formula (I) are referred to herein as "derivatives" of 3,3'-thiodipropionic acid (TDPA). Only those derivatives which are safe in contact with human skin are considered suitable for use according to the invention.

The compositions generally include a compound of formula (I) (such as TDPA) in an amount of from about 0.1% to about 5% by weight of the total composition. More typically, the compositions comprise a compound of formula (I) (eg TDPA) in an amount of from about 0.25% to about 2.5% by weight or from about 0.5 to about 1.5% by weight of the total composition. In one embodiment, the composition comprises a compound of formula (I) (eg TDPA) in an amount of from about 0.75% to about 1.25% or about 1% by weight of the total composition.

The composition may further include additional agents that impart strength to the hair, including, by way of example and without limitation, amino acids, creatine, cysteine, and ceramides. Alternatively, the composition may be free of additional hair enhancing ingredients. In certain embodiments, the composition further comprises creatine, eg, in an amount of about 0.01 to about 5% by weight. In other embodiments, the composition is substantially free of creatine, which means that the amount of creatine is insufficient to confer a measurable improvement in hair strengthening. In other embodiments, the composition is free of creatine.

Compositions of the present invention generally include a topically acceptable carrier. "Topically acceptable" means that the carrier is safe for contact with human skin. Carriers can include liquids, including single-phase, two-phase systems, or emulsions. Compositions may be aqueous or anhydrous, but are generally in the form of aqueous solutions, dispersions or emulsions, such as water-in-oil, oil-in-water, silicone-in-water, water-in-silicone, or complex emulsions. When formulated as an emulsion, emulsifiers or stabilizers are usually included. When the product is intended to be in the form of a spray, it may be desirable to employ a single phase carrier, or a dual phase carrier comprising an aqueous phase and an oily phase, including the silicone oil.

In one embodiment, the carrier includes a volatile solvent. Typically, volatile solvents may have a vapor pressure greater than about 0.01 mmHg at 20°C. Volatile solvents may include water, volatile _C5-12 hydrocarbons (such as isododecane), volatile siloxanes (such as cyclopentasiloxane), lower alcohols (such as ethanol, isopropanol, etc.), and the like. Volatile solvents may comprise up to about 99% (w/w) of the composition, more typically up to about 85% (w/w) of the composition.

The composition may comprise an oily or oily phase, which may consist of a single oil or a mixture of different oils. Suitable non-limiting examples include vegetable oils; esters such as octyl palmitate, isopropyl myristate, and isopropyl palmitate; ethers such as dioctyl ether; fatty alcohols such as cetyl alcohol, stearyl alcohol, and diethyl alcohol. Lauryl Alcohol; Isoparaffins, such as Isooctane, Isododecane, and Isohexadecane; Silicone Oils, such as Dimethicone Oil, Cyclosiloxane, and Polysiloxane ; hydrocarbon oils such as mineral oil, petrolatum, isoeicosane and polyisobutylene; natural or synthetic waxes; etc. Non-volatile silicone oils would include dimethicone and other polyalkylsiloxanes, polyarylsiloxanes, polyalkylarylsiloxanes, or mixtures thereof. Non-volatile silicone oils typically have a viscosity of about 10 to about 60,000 centistokes at 25°C and a boiling point greater than 250°C at atmospheric pressure. Non-limiting examples include dimethyl polysiloxane (dimethicone), phenyl trimethicone, and diphenyl dimethicone. Volatile and non-volatile silicone oils may optionally be substituted with functional groups such as, for example, alkyl, aryl, amine, vinyl, hydroxyl, haloalkyl, alkylaryl, and acrylate base.

The composition may include natural or synthetic film-forming polymers including, but not limited to, those that aid in styling and holding hair. Such natural polymers include shellac, alginates, gelatin, pectin, chitosan salts and cellulose derivatives. Synthetic polymers that can be used are, for example, polyvinylpyrrolidone, polyvinyl acetate, polyacrylate compounds such as acrylic or methacrylic acid polymers, base polymers of esters of these two acids with aminoalcohols or quaternary derivatives of these base polymers. Ammonized products, polyacrylonitrile and copolymers of such compounds as polyvinylpyrrolidone vinyl acetate or polyvinylpyrrolidone dimethylaminoethyl methacrylate. Other polymeric film formers include polyolefins, polyethylenes, polyacrylates, polyurethanes, silicone elastomers, silicone resins, silicone-polyalkylene oxide copolymers, silicone acrylates , polyamides, polyesters, fluoropolymers, polyethers (eg, PEG, PPG, and copolymers), polyacetates, polycarbonates, polyimides, rubbers (eg, styrene, ethylene, propylene, and/or or butene di- and tri-block copolymer elastomers), epoxy resins, formaldehyde resins, and all of the foregoing homopolymers and copolymers.

Other suitable polymeric film formers include silicone polymers, acrylates, alkacrylates, polyurethanes, fluoropolymers such as Fluomer (polyperfluoroperhydrophenanthrene) and silicone acrylates such as Acrylate/Polymer Methylsiloxane copolymer sold under the tradename KP-545 or KP 550 (Shin-Etsu). Suitable film formers include, but are not limited to, aminodipropyl dimethicone, aminopropyl dimethicone, amodimethicone, amodimethicone Oxyalkyl Hydroxystearate, Behenyl Dimethicone, C _30–45 Alkyl Dimethicone, C _24–28 Alkyl Dimethicone, C ₃₀ – ₄₅ Alkyl Methicone, Cetearyl Methicone, Cetyl Dimethicone, Dimethicone, Dimethoxysilyl Vinyl Diaminopropyl Dimethicone, Hexyl Methicone, Hydroxypropyl Dimethicone, Stearamidopropyl Dimethicone, Stearoxy Dimethicone Methicone, Stearyl Dimethicone, Stearyl Dimethicone, and Vinyl Dimethicone. Particularly preferred are silicone polymers, including polymethicones (as described in CTFA Special Publication No. 1581, which is incorporated herein by reference), polydimethylsiloxanes (such as in CTFA Special Publication No. 840, which is incorporated herein by reference) and amodimethicone (as described in CTFA Monograph No. 189, which is incorporated herein by reference).

In one embodiment, the film-forming polymer is a silicone acrylate, such as those having CTFA Special Publication No. 10082 and the INCI designation Acrylates/Dimethicone. This polymer is commercially available from ShinEtsu Chemical Co., Ltd. under the trade name KP-544. In another embodiment, the film-forming polymer may be a silicone urethane, such as those having the INCI name Dihydroxypropyl Dimethicone/SMDI Copolymer and INCI Special Publication ID No. 22006 . This polymer is commercially available from Siltech Corp. under the tradename SILMER UR-5050, which includes the polymer in isododecane.

In certain embodiments, it may be desirable to add to the composition a hydrophilic or water-soluble film former (e.g., cellulosic materials, polysaccharides, polyquaternium (such as Polyquaternium-37 (INCI), etc.) To improve spreading, emulsion stability, aesthetic look and feel, etc.

The composition may include a cationic polymer. Cationic polymers include, but are not limited to, Polyquaternium 4, Polyquaternium 6, Polyquaternium 7, Polyquaternium 10, Polyquaternium 11, Polyquaternium 16, Polyquaternium 22, Polyquaternium 28, Polyquaternium 32, and Guar Hydroxypropyltrimonium Chloride. When present, cationic polymers should generally comprise from about 0.1% to about 15% (w/w) of the composition. In other embodiments, the composition may contain an amount of cationic (quaternary ammonium) ingredients that are anhydrous or have very low levels of water (eg, less than 1% by weight). Other suitable quaternary ammonium compounds include, for example, but are not limited to, polyquaternium-37 (INCI), silicone quat-18 (INCI), PEG-2 Dimeadowfoamamidoethylmonium Methosulfate and Hexylene Glycol (INCI), and Cetrimonium Chloride (INCI). If present, such quaternary ammonium compounds should comprise from about 0.05% to about 5%, more typically from about 0.1% to about 1.5%, by weight of the total composition.

The composition may also include monomeric quaternary ammonium compounds such as alkyltrimethylammonium chlorides, dialkylmethylammonium chlorides, alkyldimethylbenzylammonium chlorides, and alkylpyridinium chlorides. chlorides).

In one embodiment, the composition comprises at least one hair conditioning agent selected from the group consisting of polyquaternium salts, cationic polymers, cationic surfactants, non-volatile dimethicone oils, dimethicone Siloxanols, Amodimethicones, Ester Oils, Fatty Alcohols, Cationic Gum and Cellulosic Substances, Amidoamines, Cetrimonium Chloride, Behenyltrimonium Chloride, Stearyl Amidopropyldimethylamine, polyesteramine, and cationic charge-modified polymers derived from guar gum, cellulose, proteins, polypeptides, chitosan, lanolin, starch, and aminosilicones.

The composition may include a nonionic surfactant, such as Laureth-23, Ceteth-10, Ceteth-20, IsoCeteth-20, Steareth-20, Oleth-10, Oleth-20, or an alkyl polydextrose. Nonionic surfactants can be formed from fatty alcohols, fatty acids, or glycerides with _C8 to _C24 carbon chains.

The composition of the present invention may further comprise proteins, peptides and amino acids, including hydrolyzed soy protein, lauryldimonium (lauryldimonium) hydrolyzed soy protein (cationic soy protein), wheat amino acids, zein, wheat protein, milk protein or Silk protein, collagen, keratin, taurine and arginine hydrochloride, etc.

The composition may also include polyols (eg, glycols) such as glycerin, propylene glycol, ethoxydiglycol, glycerol, butylene glycol, pentanediol, hexylene glycol, caprylyl glycol, and the like. These are generally added in amounts of from about 0.001 to about 5% by weight.

The composition may further include an emulsifier. The amount of emulsifier is generally from about 0.001 to about 10% by weight, preferably from about 0.01 to about 5% by weight, most preferably from about 0.1 to about 1% by weight, based on the total weight of the composition.

Emulsifiers may be of the polyethoxy type (eg polyoxyethylene ethers or esters), including chains of the form -(CH ₂ CH ₂ O) _n -. Propoxylated emulsifiers are also expected to be suitable. For example, emulsifiers that may be used in the compositions of the present invention include, but are not limited to, one or more of the following: sorbitan esters; polyglyceryl-3-diisostearate; sorbitan Alcohol monostearate, sorbitan tristearate, sorbitan sesquioleate, sorbitan monooleate; glyceryl esters such as glyceryl monostearate and glyceryl monooleate; Polyoxyethylene phenols, such as polyoxyethylene octylphenol and polyoxyethylene nonylphenol; polyoxyethylene ethers, such as polyoxyethylene cetyl ether and polyoxyethylene stearyl ether; polyoxyethylene glycol esters; polyoxyethylene Oxyethylene sorbitan ester; Dimethicone copolymer; Polyglyceryl esters such as polyglyceryl-3-diisostearate; Glyceryl laurate; Steareth–2, Steareth–10, and Steareth– 20.

Water-in-silicone emulsions are usually emulsified with nonionic surfactants (emulsifiers). Suitable emulsifiers include polydiorganosiloxane-polyethylene glycol block copolymers, including those described in US Patent No. 4,122,029, the contents of which are incorporated herein by reference. These emulsifiers generally comprise a polydiorganosiloxane backbone, usually polydimethylsiloxane, with side chains comprising -(EO) _m- and/or -(PO) _n- groups, where EO is Ethyleneoxy, PO is 1,2-propyleneoxy, the side chain is usually capped or terminated with hydrogen or lower alkyl (eg C _1-6 , typically C _1-3 ). In addition to the alkoxylated side chains, the silicone emulsifiers may also include alkyl chains pendant from the silicone backbone. Other suitable water-in-silicone emulsifiers are disclosed in US Patent No. 6,685,952, the contents of which are incorporated herein by reference. Commercially available water-in-silicone emulsifiers include those available from Dow Corning under the trade designations 3225C and 5225C FORMULATION AID; SILICONE SF-1528 available from General Electric; ABIL EM 90 and EM97, available from Goldschmidt Chemical available from Corporation, Hopewell, VA; and the SILWET ^™ series of emulsifiers sold by OSI Specialties, Danbury, CT.

Examples of water-in-silicone emulsifiers include, but are not limited to: Dimethicone PEG 10/15 Crosspolymer, Dimethicone Copolymer, Cetyl Dimethicone Oxane Copolymer, PEG–15 Lauryl Dimethicone Crosspolymer, Lauryl Methicone Crosspolymer, Cyclomethicone, and Dimethicone Copolymer, Dimethicone Copolymer (and) Caprylic/Capric Triglyceride, Polyglyceryl-4 Isostearate (and) Cetyl Dimethicone Copolymer (and ) hexyl laurate, and dimethicone copolymer (and) cyclopentasiloxane. Other examples of water-in-silicone emulsifiers include, but are not limited to, PEG/PPG-18/18 Dimethicone (trade name 5225C, Dow Corning), PEG/PPG-19/19 Dimethicone Siloxane (trade name BY25–337, Dow Corning), Cetyl PEG/PPG–10/1 dimethicone (trade name Abil EM–90, Goldschmidt Chemical Corporation), PEG–12 dimethicone Oxane (trade name SF 1288, General Electric), lauryl PEG/PPG–18/18 polymethicone (trade name 5200FORMULATION AID, Dow Corning), PEG–12 polydimethylsiloxane cross-linking polymerization (trade name 9010 and 9011 silicone elastomer blend, Dow Corning), PEG-10 dimethicone crosspolymer (trade name KSG-20, Shin-Etsu) and dimethicone Alkane PEG–10/15 crosspolymer (trade name KSG–210, Shin–Etsu).

Additional emulsifiers are provided in the INCI Ingredient Dictionary and Handbook, Eleventh Edition, 2006, the contents of which are hereby incorporated by reference.

Compositions of the invention will typically have a pH in the range 2-12, more typically 2-10. In certain embodiments, the composition will have a pH in the range of about 3 to about 7, or about 3.5 to about 6.5. The pH can be adjusted using common acid or base pH adjusters including, but not limited to, citric acid, mineral acids, ethanolamine and other amines, ammonia, sodium hydroxide, and the like.

In certain embodiments, it has been found desirable to include one or more agents that enhance the shine of hair treated with the compositions of the present invention. The gloss enhancer may be, for example, lens-shaped particles such as hemispherical PMMA, including hemispherical methyl methacrylate crosspolymers sold under the trade name 3D Tech PW (Plain) XP (Kobo). Other suitable shine enhancers include phenylpropyldimethylsiloxysilicate, polybutene, polyisobutylene, hydrogenated polyisobutylene. Silicone fluids, such as aryl-substituted siloxanes with high refractive indices, are also used as gloss enhancers. Particular mention may be made of phenyl trimethicone, which is available under the tradenames SCI–TEC PTM 100 (ISP) and PDM 20 (Wacker–Belsil), and trimethylsiloxyphenyl Polydimethylsiloxane (INCI name), available under the tradename PDM1000 (Wacker-Belsil). The PDM20 material has a refractive index of 1.437 at 25°C. The PDM 1000 material has a refractive index of 1.461 at 25°C. Another suitable silicone fluid may be trimethylsiloxyphenyl dimethicone. In general, any aryl-substituted siloxane having a refractive index greater than 1.4 at 25°C is expected to be suitable for restoring shine to hair treated with the superhydrophobic materials of the present invention. Phenylsiloxanes, such as pentaphenyltrimethyltrisiloxane or tetraphenyltetramethyltrisiloxane (commercially available as HRI fluids from Dowcorning HRI) are also used to enhance gloss. Certain organic compounds, such as octylmethoxycinnamate, can also be used to enhance shine. Shine enhancers are typically present from about 0.01% to about 5% by weight of the total composition.

In addition to the foregoing, compositions according to the invention may include pigments, pearlescent agents, and/or colorants to impart a desired color to the hair. Inorganic pigments include, but are not limited to, titanium dioxide, zinc oxide, iron oxide, chromium oxide, iron blue, and mica; organic pigments include, but are not limited to, barium, strontium, calcium or aluminum lakes, ultramarine blue, and carbon black; colorants include, but are not limited to, D&C Green #_3, D&C Yellow #_5 and D&C Blue #_1. Pigments and/or colorants may be coated or surface treated with one or more compatibilizers to aid dispersion in solvents. Preferred pigments and/or colorants are those surface-treated to render them hydrophobic.

The compositions of the present invention may optionally include other active and inactive ingredients commonly associated with hair care products. The nature and amount of these other ingredients should preferably be suitable for formulating a stable hair care product which forms a film on the keratin fibers. Preferably, these other ingredients include at least one bioactive ingredient for improving keratin fibers. Suitable additional ingredients include, but are not limited to, amino acids, antioxidants, chelating agents, colorants, softeners, emulsifiers, excipients, fillers, fragrances, gelling agents, humectants, minerals, moisturizers , light stabilizers (eg, UV absorbers), preservatives, stabilizers, colorants, surfactants, viscosity and/or rheology modifiers, vitamins, waxes, and mixtures thereof. It is contemplated that the hair care products of the present invention may also include antidandruff, deodorant, sunscreen and/or antiperspirant ingredients. In general, all such additional components should generally constitute less than 10% by weight of the composition.

The composition typically includes a preservative or antimicrobial agent, such as methylchloroisothiazolinone, methylisothiazolinone, methylparaben, propylparaben, phenoxyethanol, or caprylyl glycol.

The compositions of the present invention may be formulated in any suitable nature, including various rinse-off and leave-on formulations such as, but not limited to, shampoos, conditioners, serums, creams, sprays, lotions, gels, perfumes Creams, liquids, etc.

In one embodiment, the leave-on conditioner comprises from 0.1 to about 2.5% by weight of a compound of formula (I), such as TDPA, from about 1% to about 97% by weight of a carrier, and from about 0.01% to about 15% by weight ( together) of one or more of the following: conditioner, thickener, anionic, cationic, zwitterionic or nonionic surfactant, dimethicone oil, polyquaternium-37, panthenol , Panthenyl Ethyl Ether, Hydrogenated Castor Oil/Sebacic Acid Copolymer, Wheat Amino Acids, Phytantriol, Tocopheryl Acetate, Vinyl Dimethicone/Lauryl Dimethicone Oxyalkylene Crosspolymer, Propylene Glycol Dicaprylate/Dicaprate, Phenoxyethanol, Hydroxyethylcellulose, Capryl Glycol, PPG-1Ttrideceth-6, and Quaternium-80.

In one embodiment, the rinse-off conditioner comprises from 0.1 to about 2.5% by weight of a compound of formula (I), such as TDPA, from about 1% to about 97% by weight of a carrier, and from about 0.01% to about 15% by weight (together ) of one or more of the following: conditioners, thickeners, anionic, cationic, zwitterionic or nonionic surfactants, cetyl alcohol, dimethiconol, cetearyl alcohol, Stearamidopropyl Dimethylamine, Cetrimonium Chloride, Butylene Glycol, Diol Stearate, Wheat Amino Acids, Panthenyl Ethyl Ether, Phytantriol, Hydrogenated Castor Oil/Sebacic Acid Copolymer , tocopheryl acetate, panthenol, vinyl dimethicone/lauryl/behenyl dimethicone crosspolymer, ceteareth–20, glycolic acid, and polyethylene glycol (including PEG-90M).

In one embodiment, the shampoo comprises from 0.1 to about 2.5% by weight of a compound of formula (I), such as TDPA, from about 1% to about 97% by weight of a carrier, and from about 0.01% to about 15% by weight (together) One or more of the following: conditioners, thickeners, anionic, cationic, zwitterionic or nonionic surfactants, lauryl glucoside, sodium laureth sulfate, cocamide MIPA, Sodium Lauroyl Sarcosinate, Diol Distearate, Dimethicone, Wheat Amino Acids, Panthenyl Ethyl Ether, Phytantriol, Hydrogenated Castor Oil/Sebacic Acid Copolymer, Tocopheryl Acetate, Panthenol, Vinyl Dimethicone/Lauryl/Behenyl Dimethicone Crosspolymer, PEG–150 Pentaerythritol Tetrastearate, Guar Gum Hydroxy Propyltrimonium Chloride, Citric Acid, PEG–6 Caprylic/Capric Glycerides, PPG–12–Buteth–16, and Acrylates/C10–30 Alkyl Acrylate Crosspolymer.

The composition is advantageously applied to hair in need thereof, which means that the hair has been damaged, such as by chemical (color treatment, perm, etc.), thermal (hairdryer, curling iron, etc.) or mechanical (combing, brushing, etc.) aggression. damaged hair. Hair in need may also include hair damaged by UV light and swimming pool chemicals. In one embodiment, the composition is applied to hair that has been artificially dyed, for example with a two-part oxidation dye.

Compositions are typically applied to wet hair or damp hair (eg, hair that has been towel dried) or dry hair. The composition may be left on the hair, meaning that after application, no immediate (eg, within 1 hour of application) steps are taken to remove the composition (other than allowing the volatile components to evaporate). Compositions can also be of the other rinse-off variety, including shampoos and conditioners, which are meant to be removed substantially simultaneously with their application (eg, within 30 minutes). Other products are also contemplated, including pomades, hair gels and mousses, sprays, and the like.

The composition is usually applied for a sufficient time to improve the strength or overall appearance of the hair. This typically must be applied daily for at least three days, at least five days, at least one week, or at least two weeks, but results are expected to be seen after one application. In certain embodiments, the composition is applied to damp hair after shampooing (eg, within 30 minutes). In certain embodiments, the composition is applied to damp hair after (eg, within 30 minutes of) coloring the hair, including with a two-part oxidation dye.

specific implementation plan

Example 1

This example demonstrates that TDPA repairs damaged hair fibers as evidenced by the improvement in tensile breaking strength of hair fibers treated with TDPA. A commercial rinse-off conditioning formulation was used as the control vehicle for the study. The active formulation was prepared by adding 1% (w/w) TDPA to the control vehicle. Three samples of treated hair were prepared: untreated, treated with control vehicle, and treated with control vehicle + 1% TDPA. The treatment is applied to long, untwisted hair previously damaged by artificial coloring with oxidation dyes. This treatment was repeated five times. The overall condition of the hair fiber was determined by measuring the tensile load required to break the fiber and averaging the results for 30 fibers. The results are shown in Figure 1. Untreated hair had a break load of about 68 gm, while hair treated with the control vehicle (itself a damage repair product) showed a modest improvement over untreated hair, with a break load of about 73 gm. In stark contrast, the active formulation with 1% TDPA gave a breaking load of about 82 gm. This is associated with an improvement in tensile strength of about 20%. The recipe used in the test protocol was as follows:

The formulation of the control carrier:

Deionized water Butanediol Panthenol–DL Methylparaben Cetrimonium Chloride/Isopropanol PEG–90M cetyl alcohol Cetearyl Alcohol/CETEARETH–20 stearamidopropyl dimethylamine Ethylene glycol monostearate Propylparaben Wheat Amino Acids – AQ.PRES Phenoxyethanol Dimethiconol Hydrogenated Castor Oil/Sebacic Acid Copolymer Fragrance

glycolic acid Vinyl Dimethicone/Lauryl Dimethicone Crosspolymer – Liquid panthenyl ethyl ether Tocopheryl Acetate – SYN Phytantriol

The formulation of the control vehicle: +1% TDPA:

Deionized water Butanediol Panthenol–DL Methylparaben Cetrimonium Chloride/Isopropanol PEG–90M cetyl alcohol Cetearyl Alcohol/CETEARETH–20 stearamidopropyl dimethylamine Ethylene glycol monostearate Propylparaben Wheat Amino Acids – AQ.PRES Phenoxyethanol Dimethiconol Hydrogenated Castor Oil/Sebacic Acid Copolymer Fragrance glycolic acid Vinyl Dimethicone/Lauryl Dimethicone Crosspolymer – Liquid panthenyl ethyl ether Tocopheryl Acetate – SYN 3,3'–thiodipropionic acid Phytantriol

Claims (22)

1. A method for repairing damaged keratin fibers comprising applying to keratin fibers in need thereof a composition comprising an effective amount of a compound having the structure of formula (I) in a topically acceptable carrier to achieve sufficient improvement Time for the strength or overall appearance of the keratin fibers: Wherein, X is selected from -O-, -S-, -CH ₂ -, -NH- or -NR ^N -, wherein R ^N is methyl or ethyl, and R ₁ and R ₂ are independently selected from hydrogen, C _1–22 Hydrocarbyl groups and counter ions. 2. The method according to claim 1, wherein said keratin fibers are hair of the human scalp. 3. The method according to claim 1, wherein X is -S-. 4. The method according to claim ₁ , wherein R and R are independently selected from the group consisting of _hydrogen , alkyl, alkenyl, alkynyl, aryl, alkyl-aryl, aryl-alkyl, heteroaryl, and combinations, each optionally substituted with 1-10 heteroatoms selected from halogen, oxygen, nitrogen and sulfur. 5. _The method according to claim ₁ , wherein R and/or R are selected from C _8-22 alkyl groups. 6. The method according to claim 1, wherein R ₁ and/or R ₂ are selected from C _1-5 alkyl groups. 7. _The method according to claim ₆ , wherein R and/or R are lauryl. 8. The method according to claim ₁ , wherein R and/or R are _hydrogen . 9. _The method according to claim ₁ , wherein R1 and/or R2 are counterions selected from ammonium, quaternary ammonium, alkali metal or alkaline earth metal. 10. The method according to claim 1, wherein said compound is 3,3'-thiodipropionic acid (TDPA). 11. A method according to any preceding claim, wherein the hair of the human scalp has previously been at least one of dyed or lightened. 12. The method according to claim 11, wherein said coloring of the hair comprises treatment with a two-part oxidation dye. 13. A method according to any preceding claim, wherein the hair of the human scalp has previously been permanently treated. 14. A method according to any preceding claim, wherein the hair of the human scalp is subjected to UV damage. 15. A method according to any preceding claim, wherein the hair of the human scalp is subjected to thermal damage. 16. The method according to claim 1, wherein said compound comprises from about 0.5% to about 1.5% by weight of said composition. 17. The method of claim 1, wherein the composition includes one or more of a film former, a fluoropolymer, a gloss enhancer, a thickener, an emulsifier, a pH adjuster, or a chelating agent. 18. The method according to claim 1, wherein said composition further comprises at least one hair conditioning agent selected from the group consisting of polyquaternium salts, cationic polymers, cationic surfactants, non-volatile dimethicones Oxane Oils, Dimethiconol, Amodimethicones, Ester Oils, Fatty Alcohols, Cationic Gum and Cellulosic Substances, Amidoamines, Cetrimonium Chloride, Behenyltrimethicone ammonium chloride, stearamidopropyldimethylamine, polyesteramine, and cationic charge modifiers derived from guar gum, cellulose, protein, polypeptide, chitosan, lanolin, starch, and aminosilicone permanent polymers. 19. The method according to claim 18, wherein said composition comprises polyquaternium. 20. The method according to claim 18, wherein said composition comprises polyquaternium-37. 21. The method according to claim 18, wherein said composition is a leave-in conditioner. 22. The method according to claim 18, wherein said composition is applied to damp towel-dried or dried hair.